HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate | HCID 68468952 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate | HCID 69322462 | 48.1% |
Reaction Steps
To a stirred solution of the methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate (745 mg, 1.65 mmol) in DMF (10 ml) was added MeI (155 μL, 2.48 mmol) followed by K2CO3 (343 mg, 2.48 mmol). The reaction was stirred at ambient temperature for 3 hours, then diluted with ethyl acetate and 2M HCl. The aqueous phase was extracted with ethyl acetate, and the combined organic layers were washed with brine and dried over MgSO4. The crude mixture was purified by silica gel chromatography to give methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoate (0.368 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08492437B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-86660c43ec114e5ba9ea0bbf1e84cdb5 |
| Source note | uspto-grants-2013_07 |